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New tetra-cobaltacarborane modified zinc, cobalt and manganese phthalocyanine complexes have been synthesized via nucleophilic attack of the reference hydroxylated phthalocyanines to the oxonium adduct of cobalt bis(dicarbollide). The compounds were characterized by elemental analysis, FT-IR, 1 H NMR, 11 B NMR, UV–vis and mass spectroscopic data. Photophysical properties of zinc phthalocyanine 6 suggest that it may have potential application as dual sensitizers in the PDT and BNCT treatment of tumors. The electrochemical, in situ spectroelectrochemical and electrocolorimetric properties of these phthalocyanine conjugates were investigated together with reference phthalocyanines. In the case of electroactive Co- and Mn-phthalocyanine with cobaltacarborane substituents, in addition to ring based reduction, metal based reductions in both phthalocyanine core and cobaltocarborane units have been clearly identified. [ABSTRACT FROM AUTHOR]

Phthalonitriles and metal-free phthalocyanines substituted with 2,3-dihydroxypropoxy and [2,3,5,6-tetrafluoro-4-(2,3-dihydroxypropoxy)]benzyloxy groups were synthesized. Their complexes with phenylboronic acid were prepared in THF at reflux in the presence of molecular sieves. The new compounds were characterized by using elemental analyses, FT-IR, UV–vis, 1 H NMR, 19 F NMR, 11 B NMR, and MALDI-TOF MS spectral data. Aggregation tendency of phthalocyanine complexes in relation to their concentrations were investigated by changes in their absorption spectra. Furthermore, photophysical and photochemical properties of metal-free phthalocyanines were investigated in ethanol and dichloromethane. The fluorescence quenching properties of synthesized phthalocyanines were investigated using 1,4-benzoquinone in dichloromethane. [ABSTRACT FROM AUTHOR]

The synthesis, characterization and voltammetric and spectroelectrochemical properties of newly synthesized metallophthalocyanines (M Co, Cu, Cl–In, Cl–Mn) containing eight hexyloxy groups on non-peripheral positions together with four chloro and four 2-naphthoxy groups on peripheral positions have been presented in this work. Satisfactory yields of the phthalocyanines have been achieved by using microwave heating. The phthalocyanine derivatives have been characterized by using fourier transform infrared spectroscopy, proton and carbon nuclear magnetic resonance, mass and UV–vis spectroscopy techniques. Electrochemical studies on hexadeca-substituted phthalocyanines have been reported in this paper. In addition to typical voltammetric responses of the common octa and tetra substituted MPc’s, copper ( 3 ) and indium ( 4 ) derivatives showed completely different in situ spectroelectrochemical responses with very sharp and intense absorption bands for the anionic forms of these complexes. The aggregation behaviours of the phthalocyanine complexes were also investigated in different solvents and concentrations. [ABSTRACT FROM AUTHOR]

Novel hexadeca-substituted metallophthalocyanines (M = Cu, Ni, In) carrying eight hexyloxy groups on non-peripheral positions together with four chloro and four p -sulphonylphenoxy groups on peripheral positions have been synthesized by using microwave irradiation. All newly synthesized amphiphilic phthalocyanine complexes have been characterized by using elemental analysis, Fourier transform infrared spectroscopy, proton nuclear magnetic resonance, mass and UV–vis spectroscopy techniques. The electrochemical behavior of the phthalocyanines was investigated by cyclic voltammetry and square wave voltammetry on a platinum-working electrode. While all complexes gave common phthalocyanine ring-based electron transfer processes, changing the metal center especially affected the aggregation and chemical stabilities of the complexes during the redox reactions. Aggregation tendency of copper phthalocyanine was also studied in methanol and no aggregation was observed in the concentration range from 2 × 10 −6 to 12 × 10 −6 mol dm −3 . [ABSTRACT FROM AUTHOR]

Highlights: [•] Zinc (II) phthalocyanines bearing bulky groups were prepared and characterized. [•] Aggregation properties of these compounds were investigated in THF. [•] Aggregation is limited with the solvent rather than bulky side groups. [•] DFT-D is necessary to describe the interactions between phthalocyanines. [ABSTRACT FROM AUTHOR]

A novel multicomponent system consisting of benzene-1,4-diyldimethanimine bridged dimeric zinc-phthalocyanine groups was synthesized. Firstly, a novel unsymmetrically nitro and 2,4-di- tert -butylphenoxy groups substituted zinc (II) phthalocyanine was synthesized and then nitro group was reduced to amino functional group. All newly synthesized compounds were characterized by UV–Vis, FTIR, 1 H-NMR, MALDI-TOF MS and elemental analysis spectral data. The potential of these compounds as gate dielectric were investigated by fabricating bottom gate top contact OFET using poly 3-hexylthiophene-2,5-diyl as active layer. Field effect mobility values of 3.2 × 10 −4 cm 2 /V s was obtained when using ITO-coated glass as gate electrode. It was found that the density of leakage current was about 2 nA/cm 2 at 5 V. The capacitance density of 11.8 nF/cm 2 was achieved at a frequency of 5 Hz with slightly smaller values at higher frequency. [ABSTRACT FROM AUTHOR]

A novel unsymmetrically substituted zinc (II) phthalocyanine was synthesized through a multistep reaction sequence starting first with cyclotetramerization of 4-(4-nitrophenoxy) phthalonitrile and 4-(hexylthio) phthalonitrile, then reduction of nitro group to amino functionality and then its condensation with 1,10-phenanthroline-4-carbaldehyde. Finally, a new multicomponent ZnPc-Ru(bpy) 2 (phen) system consisting of a zinc-phthalocyanine core linked through a nonconjugated bridge to ruthenium(II) bis(bipyridine) complex was synthesized using the reaction of the phthalocyanine bearing a 4-substituted-1,10-phenanthroline subunit and [Ru(bpy) 2 Cl 2 ]·2H 2 O. The new compounds have been characterized by elemental analysis, IR, 1 H-NMR, UV–vis and MALDI-TOF MS spectral data. Intramolecular electronic interactions in these dyads were studied by absorption, and emission spectroscopy. Upon photoexcitation, these dyads exhibit intramolecular energy transfer from the Ru(II) chromophore to the ZnPc moiety. [ABSTRACT FROM AUTHOR]

Highlights: [•] Novel phthalocyanines with four 9-anthracenylmethyl esters have been prepared. [•] Aggregation tendency vs. concentration and solvent polarity has been tested. [•] Photophysical properties of novel phthalocyanine compounds have been investigated. [•] The energy transfer between anthracene substituents and Pc core was examined. [ABSTRACT FROM AUTHOR]

Abstract: The interaction of cationic photobleachable cobalt 1 and palladium 2 phthalocyanines (pcs) with calf thymus (CT) DNA was investigated by UV/vis spectrophotometric methods and gel electrophoresis. With the addition of pcs, the change in the thermal denaturation profile of DNA was observed. The results indicated that these molecules exhibit efficient DNA binding activity. The new cationic cobalt derivative 1 was characterized by elemental analysis, UV, IR and mass spectrophotometry. [Copyright &y& Elsevier]